ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 11, pp. 1846–1854. © Pleiades Publishing, Ltd., 2012. Original Russian Text © A.S. Burlov, A.S. Antsyshkina, G.G. Sadikov, V.S. Sergienko, A.I. Uraev, E.V. Korshunova, D.A. Garnovskii, T.V. Lifintseva, G.S. Borodkin, A.G. Ponomarenko, G.G. Chigarenko, I.L. Eremenko, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 11, pp. 1856–1864. 1846 Syntheses, Structure, and Tribological Study of 1-Phenyl-3-methyl-4-dodecyliminomethylenepyrazol-5-one and Its Complexes with Copper(II) A. S. Burlov a , A. S. Antsyshkina b , G. G. Sadikov b , V. S. Sergienko b , A. I. Uraev a , E. V. Korshunova a , D. A. Garnovskii c , T. V. Lifintseva d , G. S. Borodkin a , A. G. Ponomarenko e , G. G. Chigarenko e , and I. L. Eremenko b a Research Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090 Russia e-mail: garn@ipoc.rsu.ru b Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia c Southern Scientific Center, Russian Academy of Sciences, Rostov-on-Don, Russia d Pedagogical Institute of Southern Federal University, Rostov-on-Don, Russia e Scientific Industrial and Commercial Company “Don-Invek,” Rostov-on-Don, Russia Received August 18, 2011 The metal complexes of azomethine compounds occupy an important place in modern coordination chemistry [1–5] and are used as fluorescent [6–9], magnetic [10–14], catalytic [15] and optical materials [16–18]. They are used also as effective additives to lubricants [19–30]. The development of the latter is an important and urgent task. At the metal friction in an environment with complex-forming additives both chemical and tribochemical interactions occur, giving rise to the appearance on the surface of complex compounds formed from the contacting metal and ligand-additives [19–28]. Further a tribochemical processes of the complex exchange proceed: on both the rubbing surfaces a thin polymer film is formed of copper or other complex-forming transition metal. Therewith a process occurs of selective transfer, which leads to a significant improvement of tribochemical charac- teristics [31]. The effectiveness of the additives is determined by their solubility in oils, structure of the metal complexes formed, and the stability of the latter [19, 20]. To fix the metal complex on the rubbing surface, the complex coordination sphere should have a structure that minimizes the steric strains at the location of the complex in the active points of frictional contact. The steric hindrances at the location of the complex on the friction surface reach minimum when the complex has a square structure. Thus, at the selection of effective additives for lubricants the knowledge of the structure and properties of metal complexes is an important issue. In extension of the work on the synthesis of new effective additives for lubricants we have prepared 1-phenyl-3-methyl-4-dodecyliminomethylenepyrazol- 5-one (HL) and its copper complex CuL 2 (I). In the compound HL the equilibrium of the A–D tautomers can be realized [32–34]. The IR spectrum of the HL solution in hexachlorobutadiene includes the following absorption bands: a broad band at 3420 cm –1 (ν NH ) and a strong band at 1668 cm –1 (ν C=O ). The presence of a broad signal of the protons of NH group in the 1 H NMR spectrum of HL in CDCl 3 at 09.07 ppm and a doublet signal at 7.43 ppm of the (CH –NH) protons in combination with the IR spectral studies and published data [32–34] indicate the existence of HL in aminomethylene tautomeric form B with the intramolecular hydrogen bond with the oxygen atom of the pyrazole fragment. In the IR spectrum of the Cu(I) complex the absorption bands of HL at 3420 and 1668 cm –1 dis- DOI: 10.1134/S1070363212110217